Absolutely true what's been said about wearing heels in public being very different from wearing them just at home. I started off wearing cowboy boots with heels around 2.5 inches and expected everyone within 100 yards to fall about laughing. No reaction. I then put inserts in, which brought the heel up to about 4 inches. This made them feel nicer but unfortunately they put the whole boot off balance and it was difficult to walk in them without slapping the sole down. I then wore boots with block heels around 3.75 inches, and still got no reaction, so since then I've had my daily boots (4.5 inch wedge) and concealed heels (about 4 inches including a small insert). I've also worn very thin four inch wedges but they're a bit noisy so not suitable if I don't want to draw attention to myself. More people notice them, but no one has ever commented. I've also worn stiletto boots a couple of times away from home to see what reaction I got in a busy shopping centre. None!
Shoes are a bit more difficult, as there are any amount of beautiful low-cut stilettos etc, which I'd love to wear, but I want something to go with the otherwise masculine look. I have some Oxfords with block heels just under four inches, and I've worn those quite a bit, although my wife doesn't like them as they look like the shoes old ladies used to wear, in her opinion! I've tried to get out of her what shoe styles she DOES like, but got no firm answer.
I find sandals most difficult to choose and wear. Nearly all wedge sandals also have a platform, or thin straps, or both, so to get something which will blend in with my male attire is time consuming. I finally found a pair of Fly sandals with four inch wide wedge heels and (unfortunately) a one inch platform, and I wore those all the time in the summer. I have several pairs of block heel sandals about 4-4.5 inches which I'd like to try but the main thing is I'm not confident enough about their comfort to go far in them. With all of them the straps seem to dig in or rub, and I think my wife would think them a bit too feminine for her liking.
It's mainly a matter of confidence and holding your head high, walking about as though wearing heels were the most natural thing in the world. People latch on to self-confidence, just as they do to furtiveness. I now try heels on in the shop rather than sneak them off the shelf, fumble with cash payment and creep out. I put them down on the counter and make small talk with the cashier. The staff know they are for me, but they'd also know it if I were furtive. Anyway, I'm already wearing heels, so...
You'll be much more aware of different surfaces, slopes, uneven ground, etc., and you need to be careful. I'm sure my wife occasionally takes me over such ground purposely, and I've never been sure whether she does it because she knows I like it or because she's trying to make me overbalance! The biggest challenge was a hump-back bridge over a canal.
It's taken time to get to this level of confidence, so don't rush it. Just keep pushing the barriers slowly. I've never been challenged as to why I'm wearing them, but I have two kinds of answer ready depending on the kind of remark. If they're obviously just trying to embarrass me, and I think I can get away with it, I'd just say they came attached to the shoes. My second answer, which is also completely true, is that they stop backache, so I'm after the sympathy vote there! I've recently been sparring with a troglodyte on another site who calls me a perv. I've finally, today, after rather an amusing exchange, told him about my backache, so I'll see what response I get, if any. Interestingly, no one else has supported him, and this is just a mainstream social media site. Ah! a response, just before sending this message! 'Ever thought of getting medical heels?' I've asked him what they are.